


Topped with a bow

by CassielWhorechester



Category: Supernatural
Genre: Abandoned Work - Unfinished and Discontinued, Happy Dean, Incest, M/M, Mutual Masturbation, NSFW, Shower Sex, Wincest - Freeform, dean wearing womens clothing, femme!Dean, handjobs, implied wincest, man wearing womens clothes, shower handjobs, sleepy handjobs
Language: English
Status: Completed
Published: 2015-08-06
Updated: 2015-09-23
Packaged: 2018-04-13 06:35:18
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 3,209
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4511613
Author URL: https://archiveofourown.org/users/CassielWhorechester/pseuds/CassielWhorechester
Summary: <blockquote class="userstuff">
              <p>What does Dean get up to when Sam isn't around?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Hey, Cassiel here, please leave a comment if you'd like me to continue this story in any way. I'm mostly posting it the way it is because it's roughly 2 am and I just want it posted. I hope you enjoy!!

Dean was nervous all day. On edge. Just waiting for Sam to finally say he was going to head out and check out the town. Dean only waited ten minutes before driving out to the first clothing store he saw. he didn't pay attention to the name he just ran inside, grabbed a few things that he thought were roughly his size, paid- with an added 'these are for my girlfriend- before running back out to his car and then onto a store that'd sell cheap cosmetics. He grabbed what he wanted, paid, used his same excuse and ran back to baby, breaking the speed limit on his way back to the motel. He was glad no one was in the room when he got back, giving him time to do what he had been longing to do for so long.   
He went straight into the bathroom, his heart slowing at the satisfying click of the lock sliding into place. He had several bags in his hands which he quickly dropped onto the counter. He riffled through the emptiest one, pulling out a razor and shaving cream. Ladies shaving cream. His breath shook and his heart sped up again as he set the objects down and turned towards the shower. After the water was at a reasonable temperature -the water pressure wasn’t so bad either- Dean shed his clothes, grabbed his special items and stepped under the steady spray. It was a struggle for Dean to shave his legs decently. It took him almost an hour. He kept having the stop and thoroughly clean his razor of hair before moving on. But he did do it eventually. Then came his armpits. Those were still difficult but went much quicker. After finishing his shower routine, Dean shut off the water and dried off at the speed of light. He was getting a bit of an adrenaline rush from the feeling of the rough towel on his suddenly smooth legs.   
After he was dried off to the best of his ability Dean stood, naked as the day he was born, and stared at the bags full of clothing. He tried to take even breaths but even so, when he finally reached forward to start picking out an outfit his hand shook. Every piece of clothing he touched was smooth, thin and made his heart rate accelerate just a little bit. He decided to go with a cute little black skirt so he could show off his smoothened legs- show them off to who, he wasn’t leaving the hotel room and Sammy said he’d be gone all day- and a crop top turtleneck because he thought it was cute. He also grabbed his new purple thong, slipping it on right away. It felt like silk against his skin and he had to make a mental effort not to let all of his blood flow downwards. He then pulled on his skirt, struggled into his shirt and was ready to tackle the most difficult part. Makeup.  
He had watched videos of women- and men- do their makeup before and had tried it out himself once or twice. Yet the thought had his breath coming in slightly shallow pants and his hands shook worse when he reached into the flimsy shopping bag to grab the offending items. All he had gotten was some mascara, liquid eyeliner and pencil eyeliner and watermelon flavoured lip gloss. Nothing too big. Nothing that was too hard to hide in his duffle. He practically ripped open each container and got to work, taking several deep breaths before letting anything anywhere near his face. He was surprised at how many times he had to redo his left eye and irritated with the number of times he poked himself with his pencil liner. When he was done, though, he was able to look in the mirror and blush at his appearance. He looked wonderful. His green eyes slid up to his barely styled hair and a thought struck him.  
Almost forgetting, Dean gelled up his hair and grabbed the tiny black headband he had gotten. Attached to it was a large black bow that completed the whole outfit.   
“Topped with a bow…” Dean muttered to himself, watching the way his shiny lips moved in the mirror. He gathered up all of his things, slipping on a pair of flats before leaving the bathroom. The first thing he did was stuff all of his new purchases into his duffle, expertly cramming them into the very bottom. He then proceeded to toss out the garbage that had come with opening his makeup and razor. Dean slowed when he caught sight of himself in the floor to ceiling mirror that hung on the far wall of the hotel room. He struck a cute little pose, grinning and feeling...good. Dean felt really good. Until Sammy walked through the door.   
Dean’s heart dropped into his left foot and he thought he might be sick. Sam was frozen in shock, the door partly closed behind him. Neither moved. Neither breathed for what felt like years. Then Sam slowly released his grip on the heavy door, both brothers hearing it slam shut. Dean was the first to speak.  
“S-Sam, what the-what the hell are you doing back? I--” Dean was stumbling over his words, still rooted to the place he stood.  
“Dean you look…” Awful. Horrendous. Stupid. Ugly. “Amazing.” Dean’s mind short-circuited briefly.  
“Be kind, rewind?” He said dumbly. Sam laughed and took a step closer. Dean remained where he was.  
“I mean-Do you do this often? What is this? I mean, I like it whatever it is. Is this the first time you’ve done this? Does Dad know? Actually I don't care if Dad knows. Wow.” Sam rambled, taking more and more steps towards Dean, half a smile seemingly glued to his face. He was maybe one more step away from Dean when he stopped and Dean’s brain was finally able to crank out a thought.  
“N-no, dad doesn’t-dude you can’t tell him. This-This isn’t the first time. I…” Dean trailed off, begging with his eyes for his brother to understand. Sam nodded and cocked his head to the side a little bit.  
“Another question then,” Sam paused, leaving room for Dean’s heart to race back up to his ears,” Do you still want me to call you Dean or…?” This time it was Sam’s turn to trail off.  
“what? Of course. I’m not a girl Sam, I just...I like dressing this way sometimes. I don’t know. Sometimes I feel…” Dean was struggling for words, his baby brother stepping in to fill in for him.  
“Hey, you don’t need to explain it to me right now. And...I have just one more question.” Dean’s heart was starting to settle back into it’s regular place, just pounding like a jackhammer. “Can I kiss you?” Sam was blushing. Bright pink dusted right across his cheeks. Dean’s heart stopped the same time his feet started. he closed the gap between him and Sam, practically slamming his lips against the taller boy.   
Sam decided he liked the taste of watermelon. Maybe he could convince Dean to wear outfits like this more often….


	2. Morning Showers and sleepy hand jobs are sure to wake you up

**Summary for the Chapter:**

> Dean wakes up to many surprises and finds he quite likes shower time with Sam.

**Notes for the Chapter:**

> So, as requested a continuation of Dean's adventure with women's clothes, though there are significantly less clothes in this chapter. Comments and kudos are what make me keep writing!!

The next morning brought many surprises. The first one being, Dean didn’t freak out when he woke up naked and a little sore next to his, equally, naked little brother. He just looked at Sam’s peacefully sleeping face and felt a smile creep onto his own. They were close enough to breathe each other’s air. Relaxing, Dean just watched his little brother sleep for a while, trying not to over think what happened last night.

**Heat.Passion. Lips crushing lips and panting breath begging for clothes to be stripped off.**

Dean kept a smile on his face, slowly moving his hand up to gently cup Sammy’s face. He brought his lips to Sam’s nose and left a delicate peck there. **“God,f-fuck Dean. So-So--ugh--beautiful.” Sam had panted, his hips pistoning in a way that made Dean’s head spin, a dopey smile pointed up at Sam. “Don’t Call me-uhn-b-beautiful while you-you’ve got your -fuck- your dick up my ass dude.”**

Sam had laughed at that and said it again. Quieter. He called Dean so many nice things. Said he was perfect. Sam called him perfect, and beautiful and kind and amazing and it made Dean’s heart swell. It also made his ass and legs ache. Though his legs aching was technically his fault.

**“Dean, you sure you want to do it this way? Because I could--” Sam offered, seeing the slight strain for Dean to lift his knees to his chest. “Just shut up and get to** **it, Samantha.” Dean had grunted, aching for his baby brother to be inside him.**

The next surprise that came, though was that he was able to walk. He gingerly hobbled to the bathroom, passing discarded articles of feminine clothing. He was definitely going to use this to his advantage at some point. Sam really seemed to like them. Once he was in the bathroom Dean found his third surprise. His makeup was smeared to high heaven. He wasted no time in washing all of it off, scrubbing extra hard to cleanse his face. No way did he want makeup zits, even if he only put on eyeliner. Better safe than sorry. While Dean was at the sink he decided to brush his teeth and tame his hair, _then_ he decided to shower. He was still waiting for the water to warm up when he felt big hands slide over his hips. He jumped and turned his head to find his very sleepy moose, resting his Gigantor head on Dean’s shoulder.

“Sleep well last night?” Dean asked, a little nervous at how Sam would feel about last night. Sam just grumbled and kisses pretty little kisses into the crook of Dean’s neck, whispering to him about needing a shower.

“Can we just take one together?” Dean had to at least try not to get a boner at the thought. He shrugged and turned around, kissing his brother and walking into the heated water backward. Sam followed after, face practically glued to Dean’s as the shower cascaded water down on them. Sam carefully pushed Dean up against the shower wall, having to keep his face close to avoid getting water in his eyes.

“Hey come on, this was supposed to be my shower and now you’re--” Dean’s breath caught in his throat as Sam’s hand traveled downwards, grasping Dean’s half hard cock. He twisted his fist slowly, swallowing Dean’s moan with a gentle kiss. His fist began to pump faster, Dean’s breath trying to keep pace, his head thrown back leaving perfect access for Sam to begin sucking little love bites across Dean’s collarbone. Dean tried keeping a grip on Sam’s shoulders but the water made them slick and his blunt nails continuously trailed down the tender skin of Sam’s back making the younger moan softly. He rutted himself up beside Dean, hissing when Dean took him into one hand. “Let me h-help you out there.” Dean smiled cockily, his face flush, water droplets clinging to his eyelashes. With fist’s pumping and breaths coming shallow and short, the boy’s traveled higher and higher, Sam reaching his climax first. As he shouted out, his cum getting mostly sliding off Dean’s partially slick torso he gripped Dean’s cock just a little harder, sending him right over the edge with him. They panted, looking into each others eyes for a moment before letting out twin chuckles. Sam took a step back and let Dean under the less warm spray of water, turning to grab the shampoo, helping Dean suds up his hair.

“You know, we should take showers together more often.” Sam laughed at his older brother, planting a sudsy kiss to his lips. He regretted it instantly. He could taste nothing but soap.


	3. Chapter 3

**Summary for the Chapter:**

> The shortest 'what are we to each other' talk in all of history.

**Notes for the Chapter:**

> Hey, I'm really sorry for the shitty quality of this chapter. I'm going through a bought of writer's block right now and would really appreciate any ideas you guys have for future chapters. <3 <3

After showering and toweling off, Dean was faced with a choice. His normal clothes, or his girly clothes? He stared at his duffle bag while leaning against the door frame of the bathroom. Sam had already begun to change, pulling a pair of jeans on over his boxers. He caught sight of Dean’s hesitation.  
“If it helps, I didn’t have any plans to leave today.” Sam offers, hoping to ease his brother's mind. The older Winchester nods absently and practically stalked towards his bag, pausing every few feet to gather up the clothes from last night. As he finally turned back towards the bathroom with his things in hand he said,  
“Yeah, but I wanted to get some training in.” Sam couldn’t help but feel his chest deflate a bit. He pulled on his shirt and waited on the bed for Dean to finish changing. It took a while. Sam was half asleep again by the time Dean finished, walking into the room wearing a similar black skirt, flowy red crop top with matching thigh highs.  
“Uh, Dean?” Sam asked, his attention instantly peaking.   
“Wha?” Dean asked, pulling on his usual boots. “ I wanted to see how easy it’d be to hunt in a skirt.” He clarified making Sam laugh. The laugh shook right through Dean, pulling the corners of his lips towards his eyes. After gathering everything he needed- a shotgun, a pistol, several different blades and an assortment of other things- into his weapons duffle he was sprinting out the door and into the impala at lightning speeds. Sam was almost left behind, half out of breath when he slammed into the passengers seat.  
“Thanks for the warning Lightning McQueen.” Sam grumbled, rubbing drowsiness from his eyes. His hair was still wet so he debated for a minute whether or not it’d be worth the kink in his hair to pull it up into a ponytail for training. He decided he’d rather be able to see Dean and what he was doing, pulling the top portion of his hair into a tiny little ponytail atop his head. There were a few irritating strands framing his face, but Sam had learned to ignore them. They were heading far out of town, hopefully to an abandoned field where they could rough house and shoot their guns. Sam couldn’t lie when he said he was excited to rough house with his brother. That had always been his favorite part of training but now…  
“Hey Dean,” Sam said, staring out his window.  
“Yeah?” Dean asked, his voice sounding as he were far off in a daydream.  
“What are we?” He asked softly, hoping he wouldn’t regret it.  
“ You mean Human or Dancer? Because I’d say from last night you’re-” Sam pointed his bitchface at Dean, cutting him off.  
“ No, I mean, what are we to each other? Because I mean… I really don’t want to share you with anyone else…” Sam trailed off, fiddling with his fingers. Dean stopped chuckling and gave his brother a sideways glance.   
“What, you’re asking if we’re mutually exclusive? If you wanna be then I guess-I guess that’s alright.” Dean said after a short pause, his voice quivering just slightly with uncertainty. Sam perked right up, a big grin stretched across his face as leaned over and pecked Dean on the cheek. “Watch it Samsquatch, I gotta keep my eyes on the road.” Sam rolled his eyes and flopped back in his seat. A quick lick of his lips found just the slightest taste of Dean.


	4. Chapter 4

**Summary for the Chapter:**

> Sam finds out that skirts are basically magic

**Notes for the Chapter:**

> hey, guys sorry for the long wait and short chapter. I'm still in a writing funk and have been getting zero feedback!! Please let me know if you want this story to keep going!!! Comments and Kudos are the air I breathe

Training had been amazing. Dean could fight like a badass even in a skirt. Sam made sure to position himself in just the right place to see up Dean’s skirt everytime he kicked high enough. when he and Dean finally got to the wrestling it ended in sloppy make-outs and lazy grinding against each other, Dean’s skirt riding up weirdly.  
“Let’s take this back to the hotel room, my skirt is bunching up,” Dean said softly, leaving a lazy trail of kisses along Sam’s jaw. He sighed in content, helping his brother up off the ground. Trying to at least slightly adjust himself in his pants caught a snicker from Dean whom barely even showed what Sam had felt when grinding down on him.  
“What the fuck? Two seconds ago you had a boner.” Sam said with a mild laugh. Dean winked and said,  
“Still do.” Sam was mystified. Skirts were magic. From the front, you couldn’t see a thing, and from the side you could see a small bump but it could be easily passed off for a fold in the skirt. Still shaking his head Sam slammed himself into the passenger's seat, hand instantly going to Dean’s thigh. It started off mid thigh as Dean brought the engine to life but as they drove back towards the hotel it began creeping higher, making Dean’s breath come just a little shorter. He fidgeted in his seat letting out a small moan when Sam’s hand finally cupped him through his skirt. It was a tiny sound, barely audible. But Sam heard it. He lazily stroked his index finger up Dean’s bulge several times, turning Dean into a squirming mess. He was trying to keep his eyes on the road, nearly cheering when the hotel came into view. He pulled into the spot just in front of their door and told Sam to go unlock the door for him. It was almost dark and there wasn’t a person to be seen, but Dean wasn’t taking any chances. Plus, sprinting wasn’t really an option for him right now.  
Sam did as he was asked, choosing to help Dean out by getting their bags while he rushed inside. Dean had already taken off his shoes and socks and was in the process of shimmying out of his skirt by the time Sam had locked the door behind him. Dean got the skirt to his knees before Sam was suddenly there in front of him, pulling their lips together in a frantic kiss. One hand cupped Dean’s jaw and the other went straight to Dean’s panty covered cock. This time Dean’s moan was swallowed by Sam’s lips, spurring him on. He carefully helped Dean sit back on the bed, dropping to his knees in front of his big brother. Dean’s pupils were blown with lust, and his breath was quick. Sam took note of the small area of sweat around his temples. Tonight was going to be fun, Sam just hoped the taste of Dean would stain his lips...


	5. Chapter 5

Just gonna keep this short and sweet, I'm abandoning this fic for now. I've just run out of motivation and am not as interested in it anymore. I may pick it up in the future when I've got more ideas but for now this is where it ends. If you want it to continue in the future leave a comment with an idea!!! I look at all of my comments so I am sure to see it!!! <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3


End file.
